Rearrangements of organic peroxides and related processes · Elbs, Schenck, Smith, Wieland, and Story reactions is given. Unnamed rearrangements of organic peroxides and related processes
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Rearrangements of organic peroxides and related processesIvan A. Yaremenko, Vera A. Vil’, Dmitry V. Demchuk and Alexander O. Terent’ev*§
Review Open Access
Address:N. D. Zelinsky Institute of Organic Chemistry, Russian Academy ofSciences, Leninsky Prospect 47, Moscow, 119991, Russia
Scheme 111: The mechanism of the Elbs persulfate oxidation of phenols 375 affording p-hydroquinones 376.
Scheme 109: Possible transformation paths of the highly polarizedboric acid coordinated H2O2–aldehyde adduct 373.
the nucleophilic substitution of peroxide oxygen in the peroxy-
disulfate ion 378 [402] and the resulting sulfoxy group posi-
tioned in the para position (compound 379) is hydrolyzed the
with formation of p-hydroquinone 376 (Scheme 111).
Scheme 110: The Elbs oxidation of phenols 375 to hydroquinones.
The oxidation of phenols containing electron-donating substitu-
ents to dihydroxybenzenes gives products in higher yields com-
pared with phenols containing electron-withdrawing substitu-
ents (Table 17) [403-405].
The main drawback of the persulfate-mediated Elbs oxidation
of phenols, are the normally observed moderate conversions
and yields. Remarkably, under the above Elbs oxidation condi-
tions 5-hydroxy-2-pyridones 381 were prepared from pyridines
380 with good yields (Scheme 112) [406].
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Table 17: Oxidation of phenols 375a–f with potassium persulfate in the presence of alkali.
Phenol Product Yield, % Phenol Product Yield, %
375a376a
47
375d376d
69
375b376b
35
375e376e
42
375c376c
66
375f376f
49
Scheme 113: Synthesis of 3-hydroxy-4-pyridone (384) via an Elbs oxidation of 4-pyridone (382).
Scheme 114: The Schenck rearrangement.
Scheme 112: Oxidation of 2-pyridones 380 under Elbs persulfate oxi-dation conditions.
Later, the synthesis of 3-hydroxy-4-pyridone (384) via the Elbs
oxidation of 4-pyridone (382) and isolation of 4-pyridone-3-
sulfate (383) was described (Scheme 113) [407]. The synthesis
of 5-hydroxy-6-bromo-2-pyridone was described under similar
conditions [408].
1.7 Schenck and Smith rearrangementsIn 1958, Schenck observed that the storage of 5α-hydroper-
oxide 385 in chloroform for 3 days results in the shift of the
OOH group from the 5α to 7α position and a double-bond
migration with formation of 386. This reaction is nowadays
known as the Schenck rearrangement (Scheme 114) [409-411].
In 1973, Smith discovered another type of rearrangement of
allylic hydroperoxides [412]. The 7α-hydroperoxide 386 under-
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Scheme 115: The Smith rearrangement.
Scheme 116: Three main pathways of the Schenck rearrangement.
went a 20–30% isomerization to the 7β-hydroperoxide 387 if a
solution of 386 in ethyl acetate was kept at 40 °C for 48 h
(Scheme 115). This process is called the Smith rearrangement.
The mechanisms of these, at first glance simple, reactions were
systematically investigated 40 years after their discovery.
Three main pathways for the Schenck rearrangement have been
proposed (Scheme 116). Path A involves the cyclization result-
ing in the formation of a carbon-centered radical. Path B
comprises the formation of a transition state with the electron
density distributed over a cyclic system. Path C proceeds
through a dissociation to form an allylic radical and triplet
oxygen (Scheme 116) [186,413].
Path A, the initially considered most favorable pathway, was
excluded because the isomerization of hydroperoxides 388 and
389 following this route would lead to a β-scission ring opening
of 390 (Scheme 117).
However, this process was not observed and none of the
possible carbon-centered radicals 390 was trapped by molecu-
lar oxygen [414]. Meanwhile, it is known that the dioxacy-
clopentyl radical 392 formed from 391 is trapped by oxygen to
form hydroperoxide 393 (Scheme 118) [415].
It was hypothesized that the Schenck rearrangement of peroxide
394 proceeds through a cyclic structure 395 according to the
pathway shown in Scheme 119 [414].
Scheme 117: The isomerization of hydroperoxides 388 and 389.
Scheme 118: Trapping of dioxacyclopentyl radical 392 by oxygen.
However, this hypothesis was also rejected because the ESR
spectra recorded after the photolysis of 5α- and 7α-hydroper-
oxides 385 and 386 showed that the tertiary allylperoxyl radical
and secondary allylperoxyl radical are separate and distinct
species, and that they do not have the common cyclic structure
395 [416].
In a study using labeled isotope 18O2 it was found that the two
hydroperoxides 398 and 399 derived from autoxidation of oleic
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Scheme 119: The hypothetical mechanism of the Schenck rearrangement of peroxide 394.
Scheme 120: The autoxidation of oleic acid (397) with the use of labeled isotope 18O2.
Scheme 121: The rearrangement of 18O-labeled hydroperoxide 400 under an atmosphere of 16O2.
acid (397) underwent the Schenck rearrangement without incor-
porating dioxygen from the atmosphere (Scheme 120)
[417,418]. Later on, Beckwith and Davies confirmed this fact
for cholesterol hydroperoxide [416] and the hydroperoxide
generated from valencene [419].
Based on these results, no formation of triplet oxygen occurs in
the reaction, thus excluding path C in Scheme 116. Instead, a
cyclic transition state (path B, Scheme 116) became more
likely, which was confirmed by the stereoselective rearrange-
ment of optically pure olefinic hydroperoxides [420].
However, the study on the rearrangement of hydroperoxides
398, 399 obtained from oleic acid (397) using stereochemical,
oxygen-isotopic labeling and solvent viscosity analyses demon-
strated that, in hexane, a small amount of atmospheric oxygen is
incorporated into the product. The replacement of the solvent by
more viscous dodecane and then by octadecane led to a de-
creased content of atmospheric oxygen in the final product
[421,422]. These results provided evidence that the Schenck re-
arrangement proceeds also through path C in Scheme 116.
Besides, path C was also confirmed by the rearrangement of18O-labeled hydroperoxide 400 under an atmosphere of 16O2
with formation of isotopomers 401–403 (Scheme 121) [423].
Examples of the Schenck rearrangement are given in Table 18.
The Schenck rearrangement takes also place with allylic hydro-
peroxides derived from lipids. The rearrangement of the oleate-
derived allylic hydroperoxides (S)-421, and (R)-425 involved
free radicals includes the oxygen-centered radicals 422, 423,
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Table 18: Examples of the Schenck rearrangement.
Entry Allylic isomer A Allylic isomer B Ref.
1404a 404b
[424]
At 40 °C in non-polar solvents, an approximately equimolar mixture of A and B is formed
2405a 405b
[414]
In hexane, A is rearranged to an equilibrium mixture of ~80% A and ~20% B
3406a 406b
[425]
At 60–70 °C in C6H6 or MeCN in the presence of TBHN or AIBN within 16–22 h, a 50:50 A:Bmixture is formed
4
407a 407b
[426]
In CCl4 at 40 °C for 141 h, the rearrangement proceeds by 80%
5
408a 408b
[427]
In CDCl3, the rearrangement of A into B is completed in 24 h
6
409a 409b
[428]
In CDCl3, the rearrangement is completed in 72 h
7410a 410b
[429]
In C6H6 in presence of 10 equiv TBHP and 20 mol % DTBN at 40 °C for 16 h, isomers A and Bare formed in equal amounts
426, 427. The E-oleate hydroperoxide (S)-421 transforms into
the corresponding (R)-E-product 424 at room temperature with
a high (S) → (R) stereoselectivity of more than 97%. A de-
creased selectivity (~90%) was observed for product 428 ob-
tained from the Z-hydroperoxide (R)-425. In this case, the
configurational direction of the reaction was (R) → (R)
(Scheme 122) [438].
The Smith rearrangement is a free-radical chain reaction in
which atmospheric oxygen may play a greater role than in the
Schenck rearrangement. Apparently, the Smith rearrangement
proceeds through a dissociation to the allylic radical and 3O2.
Presumably, the distance between these active species is large
enough to allow an exchange with atmospheric oxygen
(Scheme 123). The Schenck and Smith rearrangements are both
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Table 18: Examples of the Schenck rearrangement. (continued)
8
411a411b
[430]
In CDCl3 the rearrangement is completed in 48 h
9
412a 412b
[431]
In CHCl3 for 5 d at room temperature, only partial conversion
10
413a 413b
[432]
In CDCl3 the rearrangement is completed after 3–4 weeks; R: CO2H, CO2Me, CH2OH, CH3
11
414a 414bIn CDCl3 the rearrangement is completed after 2–4 weeks; R: CO2H, CO2Me, CH2OH, CH3
12
415a 415b
[433]
In CDCl3 the rearrangement is completed after 2 d
13
416a 416b
[434]
In pyridine for 24 h, R: OH,CH3COO, F, Cl, conversion 12–58%
14
417a 417b
[435]
In a 5 M solution of LiClO4 in Et2O the rearrangement is completed in 24 h
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Table 18: Examples of the Schenck rearrangement. (continued)
15
418a 418b
[436]
In CDCl3/D2O, lyophilized PBS buffer at pH 7 for 20 h, the conversion is 14%
16
419a 419b
[136]
In CH2Cl2 at −78 °C with BF3·OEt2 (1 mol %)
17
420a 420b
[437]
In MeCN/H2O, only partial conversion.
Scheme 122: The rearrangement of the oleate-derived allylic hydroperoxides (S)-421 and (R)-425.
Scheme 123: Mechanisms of Schenck and Smith rearrangements.
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Table 19: Examples of the Smith rearrangement.
Entry Allylic isomer B Allylic isomer C Comments Ref.
1
429a 429b
In CDCl3 within 259 h,approximately 5% of B wastransformed into C
[427]
2
430a 430b
In CHCl3 at room temperaturewithin 150 h, the B:C ratioreached 1.8:1
[439]
3
431a 431b
In CDCl3 at 40 °C within 3.5 h, Bis transformed into C by 20%. InEtOAc at 40 °C, the yield of Cwas 25–30%
[416]
In CHCl3 after 5 d at roomtemperature, only partialconversion
[431]
4
432a 432b
In CDCl3, the B:C ratio reached1:1.5 [439]
Scheme 124: The rearrangement and cyclization of 433.
a consequence of the reversibility of the reaction of allyl radi-
cals with triplet dioxygen and differ mechanistically in the
degree of separation of these two components [186]. There are
only a few examples of the Smith rearrangement known and
some of them are collected in Table 19.
In diene or triene-containing systems (433), both the rearrange-
ment and cyclization of allylic peroxyl radicals can take place
with formation of 434–436 (Scheme 124) [440].
1.8 Wieland rearrangementIn 1911 Wieland performed the decomposition of bis(triphenyl-
methyl)peroxide (437) under an atmosphere of CO2 in boiling
xylene for 10 min and obtained the crystalline product 438 in
70% yield (Scheme 125) [441].
The mechanism of the Wieland rearrangement involves
the following three steps: Initial formation of O-centered
radical A, the rearrangement of radical A into diphenylphen-
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Scheme 126: The rearrangement of bis(triphenylsilyl) 439 or bis(triphenylgermyl) 441 peroxides.
Scheme 127: The oxidative transformation of cyclic ketones.
Scheme 125: The Wieland rearrangement.
oxymethyl radical C, and the dimerization of radical C
[442,443].
Radical 1,2-aryl migrations from silicon or germanium to
oxygen is similar to the Wieland rearrangement. The thermal
decomposition of either bis(triphenylsilyl) 439 or bis(triphenyl-
germyl) 441 peroxides leads to the rearranged products 440,
442 in high yields (Scheme 126) [444,445].
2 Unnamed rearrangements of organicperoxides and related processes2.1 Protic acid-catalyzed rearrangements of organicperoxides and related processesThe oxidative transformation of cyclic ketones 58d and 443a–d
in the reaction with hydrogen peroxide in alcohols in the pres-
ence of sulfuric acid proceeds through the formation of geminal
dihydroperoxides 444a–e. The latter compounds are oxidized to
dicarboxylic acids 445a–e followed by their transformation into
the corresponding dicarboxylates 446a–e, rather than formation
of lactones via the Baeyer–Villiger reaction (Scheme 127)
[446].
This transformation requires the following key conditions to
proceed: a reaction temperature higher than 80 °C, the H2SO4
concentration in the range of 0.2–1.0 mol/L, and a molar ratio
of hydrogen peroxide/ketone in the range of 5–10. The corre-
sponding dibutyl esters were prepared in 53−70% yields by oxi-
dation in butanol, which keeps the temperature in the range of
98−106 °C (Table 20).
In a study on the hydroxylation of compounds containing a
double bond to the corresponding α-glycols, the tungstic acid-
catalyzed reaction of cyclohexene (447) with 90% hydrogen
peroxide in methanol, ethanol, or isopropanol afforded the cor-
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Table 20: Examples of oxidation of ketones 58d, 443a–d in butanol to diesters 446a–e.
Ketone Diester Yield of diester, %
aqueous H2O2solution
ethereal solution ofH2O2
443a446a
59 64
443b446b
57 63
58d446c
62 67
443c 446d
61 65
443d 446e
64 70
responding 2-alkoxycyclohexanols 448a–c in 70, 41, and 21%
yields, respectively, as well as the trans-1,2-cyclohexanediols
449a–d (Scheme 128) [447].
Scheme 128: The hydroxylation of cyclohexene (447) in the presenceof tungstic acid.
A detailed study on the hydroxylation of cyclohexene (447) in
tert-butanol using 30% hydrogen peroxide showed that in this
reaction the formation and rearrangements of 2-hydroperox-
yalkanols 451 is involved. The treatment of 2-hydroperoxycy-
clohexanol (451) with acetone afforded the cyclic peroxide 452.
The acid-catalyzed rearrangement of the peroxide 452 gave
dialdehyde 453, which further transformed into aldehyde 454.
The isolation and characterization of the latter compound was
crucial to an understanding of the oxidation of olefins to alde-
hydes under the action of hydrogen peroxide (Scheme 129).
The study of the reactions of various unsaturated molecules
with hydrogen peroxide demonstrated that the reaction of
butenylacetylacetone 455 with H2O2 at pH 5–6 at 38–40 °C
produces 2-methyl-3-hexenoic acid (457). Other possible prod-
ucts 456 resulting from a double-bond oxidation reaction were
not observed. Apparently, the formation of carbanion A is the
driving force of this reaction. Carbanion A transforms into the
symmetrical dihydroxyperoxide B, which subsequently
rearranges through a deacetoxylation to finally afford 2-methyl-
3-hexenoic acid (457) (Scheme 130) [448].
The oxidation of bridged 1,2,4,5-tetraoxanes 458 upon heating
in an acidic medium in the presence of H2O2 is leading to esters
459 (Scheme 131) [449].
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Scheme 130: The reaction of butenylacetylacetone 455 with hydrogen peroxide.
Scheme 129: The oxidation of cyclohexene (447) under the action ofhydrogen peroxide.
It is assumed that the reaction of tetraoxanes 458a–f proceeds as
an acid-catalyzed oxidative transformation, similar to the
Baeyer–Villiger and Hock rearrangements, to yield intermedi-
ate A. This is further transformed into esters 459a–f through the
oxidation of the CH group and esterification (Scheme 132).
In another study [450], the rearrangement of isomeric ozonides
was described. Here, the ozonides 460a,b were interconverted
and rearranged into the tricyclic monoperoxide 461 under the
action of phosphomolybdic acid (PMA). This result is attribut-
able to the protic acid nature of PMA as well as its ability to
form peroxo compounds containing M–O–O groups that influ-
ence the direction of the reaction (Scheme 133).
The observed interconversion of ozonides may be useful for the
interpretation of the data on the ozonolysis of unsymmetrical
unsaturated compounds.
Scheme 131: The oxidation of bridged 1,2,4,5-tetraoxanes.
Scheme 132: The proposed mechanism for the oxidation of bridged1,2,4,5-tetraoxanes.
Carboxylic acids 464 were prepared through a camphorsulfonic
acid-catalyzed oxidative rearrangement of a 1,2-dioxolane inter-
mediate 463 prepared from malondialdehydes 462 and H2O2
(Scheme 134) [451].
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Scheme 134: The acid-catalyzed oxidative rearrangement of malondialdehydes 462 under the action of H2O2.
Scheme 133: The rearrangement of ozonides.
2.2 Lewis acid-catalyzed cleavage of peroxidesThe Lewis acid-catalyzed cleavage of peroxides follows mainly
two pathways: the O–O-bond heterolysis to form an oxycarbe-
nium ion 467 accompanied by the migration of the adjacent
substituent, and the acid-catalyzed ionization of the C–O bond
to yield carbenium ion 468. The reaction pathway is mainly de-
termined by the nature of the starting compound and the C–O
ionization pathway is promoted by the stabilization of the final
carbocation, whereas the O–O-bond heterolysis is facilitated by
a high migratory ability of the adjacent groups. The fragmenta-
tion of dialkyl peroxides 465 and ozonides 466 mainly depends
on the nature of the applied Lewis acid. In this way, SnCl4 and
BF3·Et2O facilitate the O–O-bond heterolysis (A), whereas
TiCl4 promotes the C–O ionization (SN1 mechanism) in tertiary
peroxides (B). The formation of ketones 469, 471 and ester 470
is the result of the Lewis acid-catalyzed decomposition of
ozonides through the ionization of peroxide, ionization of alk-
oxide, or oxygen–oxygen heterolysis (C) (Scheme 135) [452].
Scheme 135: Pathways of the Lewis acid-catalyzed cleavage ofdialkyl peroxides 465 and ozonides 466.
The TiCl4-promoted rearrangement of (tert-butyldioxy)cyclo-
hexanedienones 472a–d, which are generated by the ruthenium-
catalyzed oxidation of phenols with tert-butyl hydroperoxide,
provides an efficient route to 2-substituted quinones 473a–d
(Table 21) [453,454]. The mechanism of this transformation is
depicted in Scheme 136.
In the first step, the coordination of dienone 472 to the Lewis
acid gives rise to cation 474. The second step involves a 1,2-
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Table 21: TiCl4-promoted rearrangement of (tert-butyldioxy)cyclohexa-nedienones 472a–d.
Peroxide Reactionconditions
Quinone Yield,%
472a
25 °C, 1 h
473a
92
472b
−15 °C, 4 h
473b
98
472c
−78 °C, 0.5 h
473c
93
472d
−78 °C, 0.5 h
473d
91
Scheme 136: The mechanism of the transformation of (tert-butyldioxy)cyclohexanedienones 472.
alkyl migration to form cation 475. The subsequent deproton-
ation of the latter affords aromatic intermediate 476. In the final
step, trichloro-tert-butoxytitanium is eliminated from intermedi-
ate 476 to produce 2-alkylquinones 473.
The transformation of 4-methyl-4-tert-butyldioxycyclohexa-
dienone 472a into 2-methylbenzoquinone (473a) can be used
also for the regioselective synthesis of vitamin K3 477
(Scheme 137) [455,456].
Scheme 137: The synthesis of Vitamin K3 from 472a.
The use of SnCl4 or TMSOTf as the catalyst made it possible to
prepare trimethylsilyl-substituted cyclic peroxides 479a–d and
480a,b in a cis configuration starting from allyltrimethylsilane
and bicyclic [2.2.n]endoperoxides 478a–d (Table 22) [457].
The mechanism of this reaction implies that TMSOTf or SnCl4
promote the heterolytic cleavage of the C–O bond in 478d to
form carbocation 481d, which is then attacked by allyltri-
methylsilane through a chair-like transition state 482d. The
subsequent cyclization of 482d through the stabilized carbocat-
ion 483d affords silyl-substituted peroxide, 1,2-dioxane 479d,
containing the substituent (–CH2SiMe3) in the equatorial posi-
tion (Scheme 138).
The employment of BF3·Et2O as the catalyst for the rearrange-
ment of hydroperoxide 485, which is generated by the oxida-
tion of steroid 484, enables the opening of the D ring between
C-14 and C-16 to form diketone 486 (Scheme 139) [458].
2.3 Rearrangements and related processes oforganic peroxides in the presence of basesThe base-catalyzed rearrangement of cyclic peroxides 488a–g,
which are prepared by the manganese-catalyzed oxidation of 1-
and 1,2-disubstituted cyclopropanols 487a–g, provides a conve-
nient approach to the synthesis of aliphatic and arylaliphatic
α,β-epoxy ketones 489a–g. The latter compounds are attractive
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Table 22: Conditions of the synthesis of trimethylsilyl-substituted cyclic peroxides (1,2-dioxanes) 479a–d and 480a,b.
more severe conditions. Monocyclic substrates are less reactive
than bicyclic endoperoxides and require even more harsh condi-
tions.
3 Rearrangements and related processes ofimportant natural and synthetic peroxides3.1 Antimalarial, antiparasitic, and antitumor perox-idesThe extensive development of the chemistry of organic perox-
ides has been stimulated largely by the isolation of the antima-
larial agent artemisinin from leaves of the annual wormwood
Artemisia annua in 1972. The structural identification showed
that artemisinin contains a cyclic endoperoxide moiety (1,2,4-
trioxane ring), which plays a key role in its antimalarial activity
[526,527]. The highly reactive and unusual chemical structure,
in addition to low yields isolated from natural sources gave
impetus to the development of total synthesis methods of
artemisinin. Several routes towards the total synthesis of this
compound were elaborated and several semisynthetic deriva-
tives were prepared [12,16,528-533]. The high costs of these
products stimulated the search for alternative peroxides, which
are synthetically easier accessible and less expensive compared
with the natural and semisynthetic structures. It was shown that
tase and ferredoxin, use a small part of the host’s iron for their
construction. In such a manner parasite cells always contain
heme iron and non-heme iron, allows for the interaction with
artemisinin or other peroxides [542].
Numerous studies on the interaction of iron ions with
artemisinin (616) demonstrated that Fe(II) promotes the O–O-
bond cleavage via two paths. Thus, Fe(II) may bind to either O1
or O2 in artemisinin (Scheme 173) [542-551]. The interaction
of Fe(II) with O1 gives rise to an intermediate oxy radical 617a,
which undergoes β-scission to form the primary C-centered
radical 617b. The subsequent elimination of Fe(II) is accompa-
nied by the formation of compound 618 containing a tetra-
hydrofuran ring. The pathway involving the interaction of Fe(II)
with O2 affords the O-centered radical 619a. A subsequent
[1,5]-H shift results in the formation of the secondary
C-centered radical 619b, and the β-scission of the latter
produces vinyl ester 620, which can be epoxidated by the result-
ing high-valent iron-oxo species. Epoxide 621 is finally
cyclized to hydroxydeoxoartemisinin 622. The formation of 618
and 622 is evidence in favor of the proposed two pathways of
the Fe(II)-promoted transformation of artemisinin. The highly
reactive intermediates 617 and 619 apparently lead to the
damage of some parasite biomolecules [552].
The 1,2-dioxanes 623 and 624 exhibiting antimalarial activity
were isolated from the Caribbean sponge Plakortis simplex and
their reactions with Fe(II) result in compounds 625a,b and
626a,b, respectively (Scheme 174) [553].
Scheme 175 shows the mechanism including the formation of
oxygen radicals 627, 629 from cyclic peroxides 623 and 624.
The 1,5-rearrangement of the latter produces the alkyl-side
chain carbon-centered radicals 628, 630. The reaction of these
toxic intermediates with parasite biomolecules determines the
biological effect observed for 1,2-dioxanes 623 and 624
(Scheme 175).
Depending on the nature of the substituents in close vicinity of
the peroxide group, the bicyclic natural endoperoxides
G3-factors 631–633 which are involved in plant defense and
extracted from the leaves of Eucalyptus grandis, react with
Fe(II) to form different types of products. For instance, treat-
ment of the 631 with Fe(II)SO4, gives rise to 634 in 82% yield.
On the other hand the reaction of 632 under the same reaction
conditions affords three products 635, 636, and 637 in a 1:1:1
ratio. The fluorinated endoperoxide 633 gives exclusively 638
under these conditions (Scheme 176) [554,555].
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Scheme 174: The interaction of FeCl2 with 1,2-dioxanes 623, 624.
Scheme 175: The mechanism of reaction 623 and 624 with Fe(II)Cl2.
In the reaction with Fe(II), the natural antimalarial terpene
cardamom peroxide 639 isolated from Amomum krervanh
Pierre (Siam cardamom) is transformed into acids 640, 641, and
642 (Scheme 177) [164].
However, the cleavage of tetraoxane 643 gives two major prod-
ucts, namely 644 and 645, in yields of 44% and 51%, respec-
tively. The reaction mechanism based on the results of this
study is shown in Scheme 178 [556].
Presumably, in accordance with the direction from Fe(II) to O2,
tetraoxane 646 interacts with iron(II) heme 647. Starting heme
647 reacts within 30 min with formation of three products. The
LC–MS study proved the formation of the covalent coupling
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Scheme 176: The reaction of bicyclic natural endoperoxides G3-factors 631–633 with FeSO4.
Scheme 177: The transformation of terpene cardamom peroxide 639.
product 648 formed from heme (mass 616) and the tetroxane-
derived secondary C-centered radical. The molecular ion [M]+
of coupling product 648 was observed at m/z 782.3, which is
consistent with the prediction (Scheme 179) [537,556].
Under similar conditions, the same alkylated heme adduct was
obtained with trioxolanes [557]. Four peaks at m/z 782.3 were
detected which were assigned to the four possible regioisomers
of alkylated heme adduct 648 as reported for heme–artemisinin
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Scheme 178: The different ways of the cleavage of tetraoxane 643.
adducts [558]. Later, in an initial study dealing with mono-
clonal antibodies that recognize the alkylation signature (sum of
heme and protein alkylation) of synthetic peroxides it was
shown that the artemisinins alkylate proteins in P. falciparum
[559].
All the above-mentioned transformations involve the homolytic
O–O-bond cleavage resulting in the formation of an O-centered
radical, which is followed by the rearrangement into a
C-centered radical, as a key step. The subsequent transformat-
ion of the C-centered radical determines the structure of the
final product.
The peroxide, 3,6-epidioxy-1,10-bisaboladiene (EDBD, 649),
isolated from wild plants, Cacalia delphiniifolia and Cacalia
hastata, possesses cytotoxicity against the human promyelo-
cytic leukemia cell line HL60. It was shown that the mecha-
nism of biological activity of EDBD involves a rearrangement
with formation of an unstable C-centered radical intermediate
650, followed by its transformation into product 651
(Scheme 180) [560].
3.2 Rearrangement of lipid peroxidesLipids contained in cell membranes maintain the structure and
control of the vital functions of cells. Lipids are the targets of
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Scheme 179: The LC–MS analysis of interaction of tetraoxane 646 with iron(II)heme 647.
Scheme 180: The rearrangement of 3,6-epidioxy-1,10-bisaboladiene (EDBD, 649).
the reactions with reactive oxygen species (ROS) such as
various oxygen-centered radicals, which play a key role in
several pathological states [561]. Compounds containing double
bonds, polyunsaturated fatty acids and esters, cholesterol and its
derivatives easily undergo oxidation by action of oxygen-
centered radicals (Scheme 181) [562,563].
Beilstein J. Org. Chem. 2016, 12, 1647–1748.
1732
Scheme 181: Easily oxidized substrates.
Scheme 182: Biopathway of synthesis of prostaglandins.
Rearrangements of organic peroxides play an important role in
such biological processes as the synthesis of prostaglandins
from fatty acids. Prostaglandins are physiologically active
substances produced by the reaction of arachidonic acid (652)
with cyclooxygenase (COX) isoenzymes. Prostaglandin G2
(PGG2, 653) containing an endoperoxide fragment undergoes
Beilstein J. Org. Chem. 2016, 12, 1647–1748.
1733
Scheme 184: The partial mechanism for linoleate 658 oxidation.
transformations mediated by a series of specific isomerases and
synthases with production of PGE2, PGI2, PGD2, PGF2, and
TXA2 (Scheme 182) [564-567].
The formation of the metabolites isoprostanes, neuroprostanes,
phytoprostanes, and isofurans 655–657 from fatty acids under
autoxidative conditions in vivo involves both the reduction of
peroxides and their rearrangements (Scheme 183). These com-
pounds proved to be widespread in nature. Compounds
655–657 display significant biological activities, and the
isoprostanes are currently the most reliable indicators of oxida-
tive stress [568-570].
Scheme 183: The reduction and rearrangements of isoprostanes.
One of the essential fatty acids, linoleic acid, contains a homo-
conjugated diene fragment, which is responsible for a specific
peroxidation mechanism without the formation of cyclic perox-
ides. In addition to linoleic acid, its esters are present in the
human circulating low-density lipoprotein (LDL). For this
reason, the oxidation of linoleic acid esters is of special biomed-
ical interest [566]. A mechanism for linoleate (658) oxidation,
which involves hydroperoxyoctadecadienoates (HPODE,
660–662) preparation, is presented in Scheme 184. The first
step of the oxidation process is the formation of the carbon-
centered pentadienyl radical 659. The reaction of 659 with O2
produces three peroxyl radicals, one of them having a nonconju-
gated diene part with the oxygen at C-11 position. The two
other radicals have Z,E- and E,E-conjugated diene parts with
oxygen substituents at the C-9 and C-13 positions. These
peroxyl radical intermediates after abstracting hydrogen atoms
transform to the hydroperoxyoctadecadienoates (HPODE,
660–662) [570].
The Hock cleavage mechanism is a possible route to transform
lipid hydroperoxide 663 into smaller carbonyl compounds
664–666, although this transformation seems to occur only in
the presence of photosensitizers (Scheme 185) [571].
Scheme 185: The transformation of lipid hydroperoxide.
In mammalian tissues and cells, cholesterol is found to a large
extent. One of the main cholesterol functions represents to
maintaining the stability of plasma membranes. The oxidation
Beilstein J. Org. Chem. 2016, 12, 1647–1748.
1734
Scheme 186: The acid-catalyzed cleavage of the product from free-radical oxidation of cholesterol (667).
of cholesterol by means of free radical particles is responsible
for the initiation of a range of pathological conditions
[572,573]. Many processes including the rearrangement of
intermediately formed peroxides accompany the oxidation of
cholesterol. The major product of 1O2 oxidation of cholesterol
(667), cholesterol 5α-hydroperoxide (668), readily forms 5,6-
secosterol ketoaldehyde 669 and the product of its intramolecu-
lar aldolization 670 through an acid-catalyzed (Hock) cleavage
of the C5–C6 bond in 668 (Scheme 186) [67].
3.3 Rearrangement of dioxygenase enzyme–sub-strate systemsA useful chemical property of most soil bacteria concludes in
their capability to oxidize aromatic compounds. This multistep
process depends on the structure of dioxygenase enzymes,
which utilize molecular oxygen for oxidation [574]. This oxida-
tion has attracted much attention as a green chemistry approach
for the conversion of aromatic compounds to water-soluble
products and for degradation of lignin [575,576]. The ring
cleavage of 1,2-dihydroxybenzene (catechol) is likely the most
thoroughly studied reaction which is catalyzed by iron-depend-
ent catechol dioxygenase enzymes [577-579]. The oxidation of
catechols 671 and 673 by two types of enzymes – intradiol
dioxygenase and extradiol dioxygenase – affords 3-carboxy-
hexa-2,4-dienedioic acid (672) and 2-hydroxy-6-ketonona-2,4-
dienoic acid (674) (Scheme 187) [580,581].
A key step in the cleavage of the aromatic ring is the oxygen-
atom insertion into the C–C-double bond as the result of a
Criegee-like or Hock-like intermediate rearrangement
[582,583]. It was demonstrated that, despite the different mech-
anisms of the initial step of the substrate/molecular oxygen acti-
vation, both reactions produce hydroperoxide 675 as the inter-
mediate. This hydroperoxide undergoes Criegee-like or Hock-
like rearrangement through different pathways. Intradiol dioxy-
genase catalyzes the 1,2-acyl migration (path B) and the forma-
tion of an intermediate anhydride 677. On the other hand, extra-
diol dioxygenase catalyzes the 1,2-migration of the alkenyl
moiety (path A) through the intermediate formation of lactone
676 (Scheme 188) [584].
Scheme 187: Two pathways of catechols oxidation.
Therefore, the catalyst for the O–O-bond cleavage in the
Criegee-like intermediate determines the regioselectivity of the
catechol oxidation.
A similar rearrangement of the Criegee intermediate with the
cleavage of the С–С bond occurs in oxidative cleavage of
natural organic pigments, carotinoides 679 by carotenoid
cleavage dioxygenases (Scheme 189) [585,586].
In this section, we considered rearrangements of the most im-
portant natural and synthetic peroxides, which proceed or can
take place in biological systems. Apparently, there are is a much
larger number of biological processes, involving rearrange-
ments of peroxides, which has to be discovered and studied in
the future.
ConclusionThe rearrangements of organic peroxides and related processes
are covered in the literature in hundreds of publications and
several specialized reviews. However, these reviews are limited
in scope, narrow in their approach, and do not provide an
overall picture of this field of chemistry. The present review is
the first to offer a complex analysis of the available data on re-
Beilstein J. Org. Chem. 2016, 12, 1647–1748.
1735
Scheme 188: Criegee-like or Hock-like rearrangement of the intermediate hydroperoxide 675 in dioxygenase enzyme–catechol system.
Scheme 189: Carotinoides 679 cleavage by carotenoid cleavage dioxygenases.
arrangements of peroxides published in the last 15−20 years
with an excursion to the history of the discovery of particular
reactions and transformations. The rearrangements and related
processes are classified according to the type of the catalysts
used: acid- and base-catalyzed processes, reactions catalyzed by
variable-valence metals, photochemical and thermal action.
Special emphasis is drawn to current trends in the performance
and application of rearrangements of organic peroxides, such as
Beilstein J. Org. Chem. 2016, 12, 1647–1748.
1736
asymmetric synthesis, organocatalysis, and the use of transition
metal-peroxo complexes for the preparation of compounds
interesting for pharmacological applications. The published data
summarized in the review provide, for the first time, an insight
into the common and different features of the reaction mecha-
nisms and allow predicting experimental and structural require-
ments for performing rearrangements with specified results. An
analysis of the published data shows that there are numerous
new and unnamed processes related to name reactions. The de-
velopment and investigation of these processes are apparently
the future of peroxide chemistry.
Rearrangements of organic peroxides are the key steps in pro-
cesses such as the Baeyer−Villiger, the Criegee and Hock reac-
tions, the Kornblum−DeLaMare rearrangement, and Dakin and
Elbs oxidation reactions. These reactions are widely used in
chemistry: The Baeyer−Villiger oxidation is widely used for the
synthesis of esters and lactones. The Criegee reaction is em-
ployed to transform tertiary alcohols into ketones and alde-
hydes. The Kornblum−DeLaMare rearrangement is an impor-
tant tool in the synthesis of γ-hydroxy enones. The Dakin oxida-
tion is applied in the synthesis of phenols from arylaldehydes or
aryl ketones and the Elbs persulfate oxidation is used to prepare
hydroxyphenols from phenols.
The comprehensive analysis of the published data makes the
knotty term "peroxide rearrangement” more exact. Two types of
processes are actually included under the term "peroxide rear-
rangement”: processes that fall under the definition of a clas-
sical rearrangement, resulting in the formation of a compound
of isomeric structure, and processes, in which the O–O-bond
cleavage is followed by the rearrangement of one of the result-
ing fragments.
The pathways of peroxide rearrangements mainly depend on the
type of the catalysts used, the reaction conditions, and the
structure of the starting peroxide. Rearrangements can be
accompanied by a homolytic or heterolytic O–O-bond cleavage,
through the formation of a carbocation (e.g., the Criegee rear-
rangement), a carbanion (e.g., the Kornblum−DeLaMare rear-
rangement), or an O-centered radical (e.g., the Wieland rear-
rangement or rearrangements promoted by variable-valence
metals).
In recent years, there has been a growing interest in organic
peroxides as a base for the design of antiparasitic and antitumor
agents, which led to an extensive search for new classes of
peroxides. New compounds and new structural classes play a
key role in the development of the chemistry of rearrangements
and the performance of related useful transformations of perox-
ides.
AcknowledgementsThis work was supported by the Russian Foundation for Basic
Research (Grant no 16-29-10678).
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